


All Gussied Up

by SuperImposed



Series: Kinkfills: Drabbles and General Fills Edition [6]
Category: MS Paint Adventures, Problem Sleuth (Webcomic)
Genre: Crossdressing, Fluff, Kinkfill, M/M, Problem Sleuth just likes dressing up
Language: English
Status: Completed
Published: 2014-03-16
Updated: 2014-03-16
Packaged: 2018-01-15 21:23:01
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 835
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1319704
Author URL: https://archiveofourown.org/users/SuperImposed/pseuds/SuperImposed
Summary: <blockquote class="userstuff">
              <p>"So a REALLY GOOD DD/PS fic just finished up here on the meme, and I need more.</p><p>My idea is this: They've already gotten together, and Sleuth wants to go out somewhere for a nice date, but as he's new to this whole dating other men thing, he's embarrassed to be seen in public with Droog.</p><p>THE OBVIOUS SOLUTION IS TO DRESS UP LIKE HYSTERICAL DAME. And look really, really good while doing it. Droog approves.</p><p>Bonus if PS gets PI and AD to help him dress up, and they tail him and find out about his relationship with DD.</p><p>BONUS BONUS if the rest of the Crew comes along and start hitting on PS because he's hot. Slick then proceeds to flip the fuck out when he finds out that it's really PS.</p><p>I JUST NEED THIS LIKE BURNING GUYS."</p>
            </blockquote>





	All Gussied Up

**Author's Note:**

> http://homesmut.dreamwidth.org/7113.html?thread=9568969#cmt9568969  
> NOT poking fun at crossdressing or transwomen, etc.

“So....what is this about?”  
The paler figure blushed and smoothed broad hands over his pink skirt. “I wasn’t really sure how a date with another guy is supposed to go, so it helps me get into character!”  
  
Droog blinked at the sunny smile, echoing it with a softer smirk of his own. “Well you look like a doll, doll,” he murmured, offering his arm like a gentlemen. Sleuth giggled and hooked a pale hand on his elbow. The darker man quirked an invisible brow but said nothing, leading his date towards the dance hall.  
  
Sleuth tried to be cool, but in comparison to Diamonds Droog he was a chatterbox. Droog learned, with much amusement, that the detective had employed his partners’ help in choosing an outfit. A connoisseur of fine clothing himself, the carapace certainly appreciated the assistance. A pale pink flapper dress, butter yellow heels and bead bracelets, and an ivory flapper hat offset the detective’s natural paleness wonderfully, making him look even more delicate and feminine.  
  
And then they got to the dance floor.  
  
Not only was Sleuth surprisingly graceful, and unsurprisingly energetic, but the way he danced had his escort feeling a touch hot under the collar. If Droog had facial hair it would be aflame by now.

Finally he couldn’t take it any longer; Droog grabbed Sleuth’s elbow and guided him over to an empty table. Well, it was empty once Droog subtly employed the use of his elbows. He lead the panting, laughing Problem Sleuth into a seat, ordering two shots of top-shelf whiskey. The disguised detective gulped the cold drink down happily, although he did slow down enough savor some of the taste and keep his date from wincing _too_ hard.  
  
They were working on a second round, and Droog was almost considering loosening his collar, when a familiar voice caught his ear. And by ‘caught’ I mean ‘grabbed with a pair of burning tongs and dragged over broken glass’. Slick is not subtle.  
  
Droog groaned and propped his chin on one fist in lieu of a facepalm. Of all the people who could be here...oh, lovely, he’s brought Boxcars and Deuce along.  
  
“Hey Droog.” Oh gog, he was smirking. Slick walked over to the table and leaned an elbow on it. Droog’s brows quirked down the slightest bit in displeasure. “So you were on a date after all.” He grinned- no, _leered - at_ **Problem Sleuth**.  
  
Droog’s eyes widened a fraction. Slick didn’t recognize....oh, this would be bad.

“So what’s a cute girl like you doing with a square like _this_ guy?” Slick jerked a thumb back at Droog. The classier Midnight Crew member took a long pull at his drink, waiting for the fireworks. He really hoped he wouldn’t have to pull his date and his ‘boss’ apart.  
  
“Oh, I think Droog is cool!” Slick didn’t notice the brains of his gang almost choking on his booze at the girlish voice. Boxcars helpfully slapped Droog on the back.

Sleuth twisted his arms together like a little girl. “Are you a friend of his?” he tittered, batting long lashes at the mobster.  
  
“More like his boss.” Slick straightened and held out a hand. “C’mon, I can show you a better time than him any day.”  
  
Sleuth grinned mischievously. “Maybe you can,” he said, letting his voice drop back to its natural pitch, “but I’m not sure you’ll want to, Slick.”  
  
“Wha- Sleuth- the fuck-” Slick stumbled back, eyes wide. He swore some more, looking from Droog to Sleuth, utterly dumbfounded.  
  
Before he could draw a card or get back his voice, Boxcars grabbed him around the middle, hoisted him over one shoulder, smiled at Droog, and absconded.  
  
Only once Slick’s swearing could no longer be heard did Droog risk a glance at his date. Problem Sleuth had delicately placed one hand over his mouth, cheeks bulging. The moment he met Droog’s eye, he burst out laughing. It wasn’t long before the gangster joined him, tears specking his eyes by the end.  
  
“Oh....I haven’t laughed like that since....I don’t even remember.” Droog actually smiled, wiping some of the moisture from his eyes. Sleuth grinned widely.  
  
“Well I can’t remember ever hearing you laugh above a chuckle, so this has been a productive night.” He tucked a stray curl back under his hat. “Slick is never going to live this down.”  
  
“I’ll see to it personally.” Droog offered Sleuth his hand, and within moments they were back to cutting a rug.

\------

Hours later, after they had been kicked out of not one, but two closing dance halls, did the two separate. Sleuth stood on the stairs to his shitty apartment, holding Droog’s hand and smiling broadly.  
  
”Well thank you for the lovely evening”, he murmured.  
  
Droog grinned. “You look good as a girl, you know that?”  
  
“Charmer.” Sleuth leaned over for a kiss. “Goodnight.”  
  
Droog was halfway down the street when he heard Sleuth calling. He turned.  
  
“Same time next Friday?”  
  
Droog smirked.  
  
“Wear the dress.”


End file.
